Trimethylsilyldiazomethane → (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

HRID 1020986ノート

反応式

HRID 1020986 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][C@:11]([CH2:18][C:19]([CH3:21])=[CH2:20])([C:15]([OH:17])=[O:16])[CH2:10]1.[Si](C=[N+]=[N-])(C)(C)[CH3:23]>CO>[CH3:23][O:16][C:15]([C@@:11]1([CH2:18][C:19]([CH3:21])=[CH2:20])[CH2:12][C:13](=[O:14])[N:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH2:10]1)=[O:17]

参加物

4

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 58218841(S)-1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid

生成物 1

HCID 58218819(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester収率 105.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (S)-1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid (prepared from c, 430 mg, 1.49 mmol) in MeOH (5 mL) was added TMS-CHN2 (2.24 mL, 4.49 mmol, 2 M solution in hexanes) dropwise. After stirring the yellow colored clear solution at room temperature for 10 min, MeOH was removed under reduced pressure, and the solution was diluted with EtOAc (50 mL) and washed with saturated NaHCO3 solution (25 mL), water (25 mL), brine (25 mL), dried (Na2SO4) and evaporated to obtain (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (474 mg) which was used as such in next step without any further purification. LC-MS: Rt (retention time): 2.14 min, MS: (ES) m/z 302.3 (M+H+).

後処理

  1. customMeOH was removed under reduced pressure
  2. additionthe solution was diluted with EtOAc (50 mL)
  3. washwashed with saturated NaHCO3 solution (25 mL), water (25 mL), brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-c79a1ffd03804b20821a427441512110
出典データセット
uspto-grants-2014_05
特許番号
US08716494B2

反応ノート

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